Organic photoelectric material containing benzoheterocyclic structure and preparation method and application of organic photoelectric material

A technology of organic photoelectric materials and heterocycles, which is applied in luminescent materials, photovoltaic power generation, organic chemistry, etc., can solve the problems of carrier transport difficulties, carrier accumulation, device efficiency reduction, etc., and achieve improved fluorescence quantum efficiency, high Fluorescence quantum efficiency, the effect of enhancing luminous brightness

Active Publication Date: 2019-10-29
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The energy level difference of blue-light materials is generally relatively large. In order to avoid energy back-transmission, only host materials with higher energy levels than the light-emitting materials can be selected. Accumulation of flow electrons produces triplet-triplet exciton serious annihilation, that is, efficiency roll-off, which seriously affects the working life of the device
In addition, due to the wide bandgap of the blue light material itself, pure blue light / deep blue light materials usually have a lower HOMO and a higher LUMO energy level. The potential barrier of the carrier leads to the increase of the driving voltage, the difficulty of carrier transport, and the decrease of the balance; Pure (greater than 470nm), will also cause a reduction in device efficiency

Method used

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  • Organic photoelectric material containing benzoheterocyclic structure and preparation method and application of organic photoelectric material
  • Organic photoelectric material containing benzoheterocyclic structure and preparation method and application of organic photoelectric material
  • Organic photoelectric material containing benzoheterocyclic structure and preparation method and application of organic photoelectric material

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Experimental program
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Effect test

Embodiment 1

[0039] Example 1: The above compound 1 of the present invention can be synthesized by the following method.

[0040]

[0041] In a 500ml reaction flask, phenanthrenequinone (20.80g, 100mmol), 6-amino-1,4-benzodioxane (16.63g, 110mmol), 1-naphthaldehyde (17.18g, 110mmol), ammonium acetate (15.41g, 200mmol) was dissolved in 250g (based on the mass of phenanthrenequinone) and added to the reactor. Under a nitrogen atmosphere, the temperature was raised to 115°C for 8 hours. The liquid phase monitoring showed that there was no remaining phenanthrenequinone, cooled to room temperature, and washed with ethanol Beat once with ethanol:ethyl acetate at a volume ratio of 10:1 to obtain 40.20 g of the target compound with a yield of 84%. The quality is characterized as follows: mass spectrometer MALDI-TOF-MS (m / z) = 478.5514, the theoretical molecular weight is 478.5510; Anal.CalcdforC33H22N2O2 (%): C82.83, H4.63, N5.85, Found: C82.81, H4 .65, N5.85.

Embodiment 2

[0042] Embodiment 2: above-mentioned compound 22 of the present invention can be synthesized by following method.

[0043]

[0044]In a 500ml reaction flask, phenanthrenequinone (20.80g, 100mmol), 6-amino-1,4-benzodioxane (16.63g, 110mmol), 1-pyrenecarbaldehyde (25.55g, 110mmol), ammonium acetate (15.41g, 200mmol) was dissolved in 250g (based on the mass of phenanthrenequinone) and added to the reactor. Under a nitrogen atmosphere, the temperature was raised to 115°C for 8 hours. The liquid phase monitoring showed that there was no remaining phenanthrenequinone, cooled to room temperature, and washed with ethanol Beat once with ethanol:ethyl acetate at a volume ratio of 10:1 to obtain 44.21 g of the target compound with a yield of 80%. The compound is characterized as follows: mass spectrometer MALDI-TOF-MS (m / z)=552.6338, theoretical molecular weight is 552.6330; Anal.CalcdforC 39 h 24 N 2 o 2 (%): C84.76, H4.38, N5.07, Found: C84.75, H4.40, N5.06.

Embodiment 3

[0045] Example 3: The above compound 31 of the present invention can be synthesized by the following method.

[0046]

[0047] In a 500ml reaction flask, phenanthrenequinone (20.80g, 100mmol), 1,4-dimethyl-1,2,3,4-tetrahydroquinoxalin-6-amine (19.50g, 110mmol), 1- Anthracene formaldehyde (22.69g, 110mmol) and ammonium acetate (15.41g, 200mmol) were dissolved in 250g (based on the mass of phenanthrenequinone) of acetic acid and added to the reactor. Under a nitrogen atmosphere, the temperature was raised to 115°C for 8 hours, and the liquid phase monitoring There was no remaining phenanthrenequinone, cooled to room temperature, and beating once with ethanol: ethyl acetate with a volume ratio of 10:1 to obtain 43.26 g of the target compound with a yield of 78%. The compound is characterized as follows: mass spectrometer MALDI-TOF-MS (m / z)=554.6968, theoretical molecular weight is 554.6970; Anal.CalcdforC 39 h 30 N 4 (%): C84.45, H5.45, N10.10, Found: C84.44, H5.48, N10.08....

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Abstract

The invention belongs to the field of the photoelectric material application technology, and particularly relates to an organic photoelectric material containing a benzoheterocyclic structure and application of the organic photoelectric material. According to the organic photoelectric material, polycyclic aromatic hydrocarbon is introduced into a nitrogen atom site of a five-membered heteroaromatic ring of phenanthroimidazole and a benzo-ester heterocycle is introduced into a carbon atom site at the same time, the organic photoelectric material is a material of which a single triplet state energy gap delta E<ST> is smaller and the triplet state energy level of a receptor is twice higher than that of a single excited state, and an electroluminescence mechanism of an RISC and TTA coexistingsystem provides a feasible path to obtain high photoelectric conversion efficiency and solve the current problems of roll-off of efficiency and light color quality of a dark blue fluorescent material.The organic photoelectric material containing the benzoheterocyclic structure independently exhibits excellent performance as a luminescent layer material or as a luminescent layer doping material inan organic electroluminescent device through the selection and structural design of a donor/receptor, the synthesis process and purification process are simple, and the organic photoelectric materialcan be applied to industrial production.

Description

technical field [0001] The invention belongs to the field of photoelectric material application technology, and in particular relates to an organic photoelectric material containing a benzoheterocyclic structure, a preparation method and application thereof. Background technique [0002] Organic electroluminescent device (OLED) is a new display technology with ultra-thin, high brightness, wide viewing angle, self-illumination, low power consumption, low cost, bendable and low temperature conditions (the liquid crystal in TFT-LCD is in It will solidify under such conditions) and can work normally. It is praised by the industry as the ideal and most promising next-generation display technology after LCD. [0003] As one of the three primary colors, blue light has been lagging behind the development of green and red OLEDs, and there are many problems that need to be solved, which is determined by the nature of blue OLED itself. Whether it is fluorescent or phosphorescent mater...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/00C07D403/04C07D411/04C07D409/04C07D413/04C07D417/04C07D401/04C07D421/04C09K11/06H01L51/50H01L51/54H01L51/42H01L51/46
CPCC07D405/00C07D403/04C07D411/04C07D409/04C07D413/04C07D417/04C07D401/04C07D421/04C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1096H10K85/622H10K85/615H10K85/6576H10K85/6574H10K85/657H10K30/00H10K85/6572H10K50/00Y02E10/549
Inventor 穆广园庄少卿任春婷
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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